ethyl 3-(6-methoxy 7-methyl benzo[d][1,3]dioxol-5-yl)-(E)-2-propionate | 918896-33-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-(6-methoxy 7-methyl benzo[d][1,3]dioxol-5-yl)-(E)-2-propionate
• 英文别名: ethyl (E)-3-(6-methoxy-7-methyl-1,3-benzodioxol-5-yl)prop-2-enoate
• CAS: 918896-33-0
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: HBGOHHISKZEDCM-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(6-methoxy 7-methyl benzo[d][1,3]dioxol-5-yl)-(E)-2-propionate 在 AD-mix-α 、 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 24.0h， 生成 ethyl 2-azido-(3S)-hydroxy-3-(6-methoxy-7-methyl-benzo[d][1,3]dioxol-5-yl)-(2S)-propionate
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056
• 作为产物：
  描述：

  3,4-Methylendioxy-phenyl-formiat 在 盐酸 、 氢氧化钾 、 正丁基锂 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 41.42h， 生成 ethyl 3-(6-methoxy 7-methyl benzo[d][1,3]dioxol-5-yl)-(E)-2-propionate
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056

文献信息

• Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions
  作者：S. Chandrasekhar、N. Ramakrishna Reddy、Y. Srinivasa Rao

  DOI：10.1016/j.tet.2006.09.056

  日期：2006.12

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.